Reaction condensation products of tertiary alkyl ureas and formaldehyde and methods for producing the same



Patented Aug. 20, 1946 UNITED STATES PATENT OF 6 218 FlCE];

TERTIARY ALKYL UREAS AND FORMAL- DEHYDE AND METHODS FOR PRODUCING THE SAME Mortimer T. Harvey, South Orange, N. J., and

Solomon Caplan, New York, N. Y., assignors to Harvel Research Corp New Jersey oration, a corporation of No Drawing. Application May 31, 1943,

' Serial No. 489,194.

2 Claims. (Cl. zoo-s9) 1 This invention relates to novel compositions of matter and to methods for preparing the same. In its more specific aspect the invention is directed to the organic condensationreaction products obtained by reacting certain amides with formaldehyde and methods for preparing the same,

more than 1 mole of formaldehyde and preferably at least two and between two and three moles of formaldehyde for each mole of said monoter- 'tiary alkyl ureas in the presence of a smallamount of an acidic or basic catalyst to hasten the reaction. This mixture may be heated to boiling, and maintained in this state of boiling under a reflux condenser until the organic confifteen minutes. I

' ucts. We have further" discovered that novel densation reaction product is produced. This product may be dried and is soluble in ethyl alcohol, mixtures of butyl alcohol and toluol and Other solvents. v

For a fuller understanding of the objects and nature oi'this invention, attention is directed to" the following specific examples which are given by way of illustration:

Example 1 Tertiary butyl urea grams 116 Formaldehyde solution (37 /2%) d0 100 and non-tacky solid. A 5 to 10 gramsample 01'- said mixture may be converted to said dry, nonabout] Ammonia solution (26) cc '2.7

This mixture was refluxed at boiling temperature for one hour and allowed to cool.

Example 2 Tertiary butyl urea "grams..- 116 Formaldehyde s lution (W /3%) -do 160 Ammonia solution (26) cc 2.7

This mixture was refluxed at boiling temperature for one hour and allowed to cool. 3

Example 3 Tertiary butyl urea grams 116 Formaldehyde solution (37V2%) do.. 240 Ammonia solution (26") cc 2.7

This mixture was refluxed at boiling temperature for one hour and allowed to cool.

Examples 4, 5 and 6 v The above series was repeated but instead oi 116 gramsof tertiary butyl urea, tertiary amyl urea was used.

130 grams of i 00 two hours at 105 C.

Examples 7, 8 and 9 Examples 1, use, of 144 grams of tertiary hexyl urea instead of the 116 grams of tertiary butyl urea.

Example 10 About 30 grams of mono tertiary buty1urea,1201 I cc. of formaldehyde, 40% water solution, and 6 cc. of NH4OH 28 Baum were heated to ebullition for about one hour, after. which. cc. of

butyl alcohol and 3 cc. 0: H3PO4 were added and l i the whole heated under a reflux condenser. This material is suitable as a surfacev coating and as an impregnating medium, and can be set after application by heating at about 270 F.1or about These novel products find application in .various fields and may be used to provide novel prodproducts may be obtained by reacting formaldehyde with a mixture-of one or more ofsaid mono tertiary alkyl ureas andother compounds as urea and the like.

These formaldehyde-tertiary alkyl urea organic condensation reaction products hereinbeiore described are non-oily and are'thick and viscous, like-heavy molasses and when added to the normally thinliquid organic condensation reaction I products of urea-formaldehyde in water, in the proportion of about 4. parts by weight of the former to about 1 part by weight Ofthe latter,

this admixture may be beat convertedto a dry tacky, solid state by heating the same for The .entire disclosures embodied in our copendingapplications Serial No. 294,480 filed September 12, 1939, and Serial No. 463,132, filed October 23, 1942, are hereby made part of-this application and thus are embodied herein, I

This application is a continuation in part of our application 463,132, through 294,480 to our application Serial No. 217,220 filed July 2, 1938.

Having thus described our invention, what we claim and desire to protect by LetterspPatent is:

1. The organic condensation reaction product produced by heating a mixture of formaldehyde and a mono tertiary alkyl urea having i'our six carbon atoms in the alkyl group, the mole ra-, tio of the former to the latter in said mixture being between about 1-1 and 6 1. v

2. The method comprising by the application of heat reacting iormaldehyde'with a mono ter-- tiary alkyl urea having from 4 to 6 carbon atoms in the alkyl group, the mole ratio of the former to the latter being greater than 1 to 1 and no greater than 6 to 1.

- MORTIMER T. HARVEY.

SOLOMON CAPLAN.

2 and 3 were repeated but with the i such 

